H&M has really comfortable leather leggings, which you can find here. You really need a long flowing blouse to balance out the edginess of the leggings, mine is from Artizia and you can find some of their fall colors here. Zara has some really wonderful blazer options and I loved this black one.
looking amazing, per usual!! wish i was still in chicago so we could share closets like in college…miss you!